Tag: M.W=100-200

Reference of 32692-19-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 5-nitro-2,3-dihydro-lH-mdole (1.0 g, 6.1 mM) in DMF is treated with CsCO3 (3.0 g, 9.1 mM) and 2-Chloro-N,N-diethyl-acetamide (1.1 g, 7.3 mM) and heated to 8O0C for 16 hours. The solution Is cooled, poured into water, extracted with EtOAc, the organic layer separated, dried (MgSO4) and the solvent removed at reduced pressure. The residue is recrystallized from EtOH. This solid is suspended in EtOH, treated with 10% Pd/C (0.2 g) and the reaction hydrogenated on a Parr Shaker at 50 psi for 2 hours. The reaction is then filtered and the solvent removed at reduced pressure to give the product as a gray solid (0.8 g, 13%). LC/MS 0.46 min. 249 (M+H, 100%); IH-NMR (300 MHz, DMSO-d6) delta 6.56 (m, IH), 6.51 (m, IH), 6.45 (s, IH), 3.80 (bs, 2H)5 3.62 (s, 2H), 3.30 (m, 2H), 3.26 (m, 4H), 2.91 (m, 2H), 1.21 (s, 3H), 1.20 (s, 3H).

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2007/97697; (2007); A1;,
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Application of 1504-06-9, These common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: 3-methyl-3-(pyrimidin-5-ylmethyl)-l ,3-dihydro-2H-indol-2-onePyrimidin-5-ylmethanol (510 mg, 4.63 mmol) in tetrahydrofuran (8 mL) at room temperature was treated with sodium hydride (185 mg, 4.63 mmol) and stirred for 5 minutes, sodium salt precipates out of solution. p-Toluenesulfonyl chloride (883 mg, 4.63 mmol) was added and the mixture stirred for one hour, to form pyrimidin-5-ylmethyl 4-methylbenzenesulfonate. In a separate flask 3-methyloxindole (682 mg, 4.63 mmol) and A^V-dimethylethylenediamine (1.538 mL, 10.19 mmol) in tetrahydrofuran (16 mL) were cooled to -78 0C and treated dropwise with n-butyllithium (2.5M in hexanes, 4.08 mL, 10.19 mmol). The mixture was allowed to warm to O0Cand stirred for 15 minutes. The mixture was recooled to -78 0C. To this mixture, the tetrahydrofuran solution of pyrimidin-5-ylmethyl 4-methylbenzenesulfonate was added via cannula and the mixture was allowed to warm to room temperature and stirred for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/isohexane to afford 3-methyl-3-(pyrimidin-5-ylmethyl)-l,3- dihydro-2H-indol-2-one as a white solid.1H NMR (CDCl3): delta 8.97 (s, 1 H), 8.29 (s, 2 H), 7.88 (br s, 1 H), 7.25(d, 1 H, J=7.3 Hz), 7.20 (m, IH), 7.11 (m, 1 H)5 6.74 (d, 1 H, J=7.8 Hz), 3.20 (d, 1 H, J=13.5 Hz), 3.0 (d, 1 H, J=13.5 Hz), 1.57 (s, 3H) MS: m/e 240.19 (M + H)+

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16800-68-3 as follows. Recommanded Product: 1-Acetylindolin-3-one

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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Electric Literature of 112656-95-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 112656-95-8, name is 7-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Add 7-nitroisatin 3 (10g, 0.052mol) and tetrahydrofuran (200mL) to a 250mL reaction flask, add sodium borohydride (2.4g, 0.061mol) in portions, and add tetrachloride in portions under cooling in an ice bath. Zirconium (42.4 g, 0.182 mol).The temperature was raised to room temperature for 18 hours, and the starting material disappeared by HPLC.1 mol / L hydrochloric acid (50 mL) was slowly added dropwise to the reaction flask, stirred for 30 minutes, ethyl acetate (100 mL) was added, 100 mL of water was added, insoluble matter was filtered off, the filtrate was left to separate and the organic layer was washed with 100 mL of water, and concentrated A yellow crude product was obtained, which was recrystallized from ethyl acetate and n-heptane to obtain 7.2 g of yellow crystals with a yield of 86% and a purity of 98.2%.

The synthetic route of 7-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Suli Fine Chemical Co., Ltd.; Wang Jingli; Yang Kai; Fei Zhongbo; Cao Wenli; Wang Liyang; Ding Shaocong; (6 pag.)CN110845388; (2020); A;,
Indoline – Wikipedia,
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334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H7NO3

A mixture of 5-(3-aminopyrrolidin-l-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4- Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; LOWRIE, JR., Lee Edwin; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; PADILLA, Fernando; WANNER, Jutta; XIE, Wenwei; ZHANG, Xiaohu; WO2012/130780; (2012); A1;,
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Application of 100510-65-4, The chemical industry reduces the impact on the environment during synthesis 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, I believe this compound will play a more active role in future production and life.

EXAMPLE G N-Propyl-N’-[2,3-dihydro-3,3-dimethyl-2-oxo-(1H)-indol-6-yl]-urea 3.52 g. (0.02 mole) 6-amino-2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one are suspended in 40 ml. anhydrous dioxan and mixed at ambient temperature within the course of 10 minutes with a solution of 1.7 g. (0.02 mole) n-propyl isocyanate in 10 ml. dioxan, whereupon a clear solution is formed. Shortly thereafter, the product begins to separate out as a crystalline mass. After 1 hour, the suspension is mixed with ligroin and the precipitate is filtered off with suction, washed with ligroin and diethyl ether and recrystallized from ethanol. Yield 3.91 g. (75% of theory); m.p. 223-225 C.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Amino-3,3-dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Mannheim GmbH; US4985448; (1991); A;,
Indoline – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89-40-7, name is 5-Nitroisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H4N2O4

General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15mol% Co/C-N-X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm ¡Á 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Wang, Xi; Li, Yingwei; Journal of Molecular Catalysis A: Chemical; vol. 420; (2016); p. 56 – 65;,
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Electric Literature of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by N-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide N-[(5-chloro-1,3-dioxo-2-isondolinyl)methyl]-N-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSO-d6): delta (ppm)=4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J=9.1 Hz, 2H), 7.22 (d, J=9.1 Hz, 2H), 7.90 (d, J=1.2 Hz, 2H), 7.97 (t, J=1.2 Hz, 1H), 12.71 (br s, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=51.77 (CH2), 54.72 (CH2), 114.39 (2CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO).MS (+ESI): m/z=379 (M+H).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
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Application of 1504-06-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1504-06-9, name is 3-Methyloxindole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

The chemical industry reduces the impact on the environment during synthesis 3-Methyloxindole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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Electric Literature of 56341-39-0,Some common heterocyclic compound, 56341-39-0, name is 6-Fluoroindolin-2-one, molecular formula is C8H6FNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1-(6-Fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 6-Fluoro-1,3-dihydro-indol-2-one was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 299.2 [M++1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
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